ES2268269T3 - Complejos cobre-carbeno y su uso. - Google Patents

Complejos cobre-carbeno y su uso. Download PDF

Info

Publication number: ES2268269T3
Authority: ES; Spain
Prior art keywords: alkyl; mmol; copper; aryl; formula
Prior art date: 2003-01-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES03029974T

Other languages

English (en)

Spanish (es)

Inventor

Klaus Dr. Kunz

Ulrich Dr. Scholz

Oiiver Dr. Gaertzen

Dirk Ganzer

Joachim Dr. Wesener

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lanxess Deutschland GmbH

Original Assignee

Lanxess Deutschland GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-01-07

Filing date

2003-12-30

Publication date

2007-03-16

2003-12-30 Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH

2007-03-16 Application granted granted Critical

2007-03-16 Publication of ES2268269T3 publication Critical patent/ES2268269T3/es

2023-12-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims abstract description 81
-1 1,2-ethenediyl moiety Chemical group 0.000 claims abstract description 49
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 24
125000003118 aryl group Chemical group 0.000 claims abstract description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001879 copper Chemical class 0.000 claims abstract description 17
239000001301 oxygen Substances 0.000 claims abstract description 17
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
239000003446 ligand Substances 0.000 claims abstract description 15
125000005842 heteroatom Chemical group 0.000 claims abstract description 13
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000004354 sulfur functional group Chemical group 0.000 claims abstract description 8
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 50
150000001875 compounds Chemical class 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 34
125000002947 alkylene group Chemical group 0.000 claims description 19
238000000034 method Methods 0.000 claims description 17
239000002585 base Substances 0.000 claims description 16
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(II) bromide Substances [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 16
125000001188 haloalkyl group Chemical group 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000010949 copper Substances 0.000 claims description 9
229910052802 copper Inorganic materials 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 7
229910019142 PO4 Inorganic materials 0.000 claims description 6
235000021317 phosphate Nutrition 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000007942 carboxylates Chemical class 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
238000000227 grinding Methods 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910002651 NO3 Inorganic materials 0.000 claims description 3
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 2
101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000001345 alkine derivatives Chemical class 0.000 claims description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000012954 diazonium Substances 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 2
150000002222 fluorine compounds Chemical class 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
150000004820 halides Chemical group 0.000 claims description 2
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 claims description 2
YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 58
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
239000000047 product Substances 0.000 description 36
238000005859 coupling reaction Methods 0.000 description 35
230000008878 coupling Effects 0.000 description 34
238000010168 coupling process Methods 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 30
229910052786 argon Inorganic materials 0.000 description 29
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 28
WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000004440 column chromatography Methods 0.000 description 17
239000000284 extract Substances 0.000 description 17
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
IGISPMBUGPHLBY-UHFFFAOYSA-N 1-iodo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(I)=C1 IGISPMBUGPHLBY-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
238000004458 analytical method Methods 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 13
238000012545 processing Methods 0.000 description 13
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
229910000024 caesium carbonate Inorganic materials 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 10
239000012043 crude product Substances 0.000 description 10
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 10
125000005259 triarylamine group Chemical group 0.000 description 9
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 6
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000004450 alkenylene group Chemical group 0.000 description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
125000002971 oxazolyl group Chemical group 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
239000012634 fragment Substances 0.000 description 3
125000002541 furyl group Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical compound CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 2
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
ZMCUDHNSHCRDBT-UHFFFAOYSA-M caesium bicarbonate Chemical compound [Cs+].OC([O-])=O ZMCUDHNSHCRDBT-UHFFFAOYSA-M 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 2
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
229910000064 phosphane Inorganic materials 0.000 description 2
150000003002 phosphanes Chemical class 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000000719 pyrrolidinyl group Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000005837 1,2-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([*:2])C1([H])[H] 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
PJOUURZOYJMYPA-UHFFFAOYSA-N OClC#N Chemical compound OClC#N PJOUURZOYJMYPA-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
YNYHGRUPNQLZHB-UHFFFAOYSA-M copper(1+);trifluoromethanesulfonate Chemical compound [Cu+].[O-]S(=O)(=O)C(F)(F)F YNYHGRUPNQLZHB-UHFFFAOYSA-M 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000004428 fluoroalkoxy group Chemical group 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 description 1
125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
IXHWPHKAIWPAKX-UHFFFAOYSA-N pyridine;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=NC=C1 IXHWPHKAIWPAKX-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000012549 training Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyridine Compounds (AREA)
Catalysts (AREA)

ES03029974T 2003-01-07 2003-12-30 Complejos cobre-carbeno y su uso. Expired - Lifetime ES2268269T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10300098		2003-01-07
DE10300098A DE10300098A1 (de)	2003-01-07	2003-01-07	Kupfer-Carben-Komplexe und ihre Verwendung

Publications (1)

Publication Number	Publication Date
ES2268269T3 true ES2268269T3 (es)	2007-03-16

Family

ID=32478149

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES03029974T Expired - Lifetime ES2268269T3 (es)	2003-01-07	2003-12-30	Complejos cobre-carbeno y su uso.

Country Status (6)

Country	Link
US (1)	US20040192664A1 (de)
EP (1)	EP1437355B1 (de)
CN (1)	CN1517351A (de)
AT (1)	ATE331721T1 (de)
DE (2)	DE10300098A1 (de)
ES (1)	ES2268269T3 (de)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200813014A (en) *	2002-03-28	2008-03-16	Astrazeneca Ab	Quinazoline derivatives
US8318752B2 (en) *	2003-09-19	2012-11-27	Astrazeneca Ab	4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(N-methylcarbamoyl-methyl)piperidin-4-yl]oxy}quinazoline, its pharmaceutically acceptable salts, and pharmaceutical compositions comprising the same
DE602004014190D1 (de) *	2003-12-23	2008-07-10	Lundbeck As Valby H	2-(1h-indolylsulfanyl)-benzylaminderivate als ssri
AR052308A1 (es) *	2004-07-16	2007-03-14	Lundbeck & Co As H	Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto
US7078362B2 (en) *	2004-12-09	2006-07-18	Equistar Chemicals, Lp	Carbene donor-modified Ziegler-Natta catalysts
US7629473B2 (en) *	2005-06-17	2009-12-08	H. Lundbeck A/S	2-(1H-indolylsulfanyl)-aryl amine derivatives
AR054393A1 (es) *	2005-06-17	2007-06-20	Lundbeck & Co As H	Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos.
DE102008022788A1 (de)	2008-05-08	2009-11-12	Süd-Chemie AG	2,6-Pyrazinverbrückte Carbenkomplexe
MY183041A (en) *	2008-05-13	2021-02-08	Astrazeneca Ab	Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- {[1- (n-methylcarbamoylmethyl) piperidin- 4-yl] oxy}quinazoline
US8580394B2 (en)	2009-11-19	2013-11-12	Universal Display Corporation	3-coordinate copper(I)-carbene complexes
RU2502724C1 (ru) *	2012-10-22	2013-12-27	Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации	Способ получения нитродифениламинов
CN103396356B (zh) *	2013-08-12	2015-04-15	宁波大学	螺芴吡啶铜微纳米粒子及其制备方法
EP3054936B1 (de)	2013-10-10	2023-10-18	Eastern Virginia Medical School	4-((2-hydroxy-3-methoxybenzyl)amino)benzolsulfonamid-derivate als 12-lipoxygenase-inhibitoren
CN104327007B (zh) *	2014-10-20	2016-07-27	安徽师范大学	3,4,5-三取代噁唑烷酮类化合物及其制备方法
US10506723B2 (en)	2014-12-02	2019-12-10	International Business Machines Corporation	Enhanced substrate includes a carbene-coated metal foil laminated to a substrate that includes glass fiber impregnated with a base polymer
CN104668577B (zh) *	2015-02-05	2019-01-15	宁波大学	一种镍微纳米粒子及其制备方法
KR102048115B1 (ko) *	2016-12-15	2019-11-22	국민대학교산학협력단	공유결합성 유기골격체
CN106588669B (zh) *	2017-01-13	2018-09-11	南京工业大学	一种利用微通道反应系统连续制备硝基苯甲醚的方法
CN114146729B (zh) *	2021-11-16	2023-01-17	大赛璐（中国）投资有限公司	一种双齿卡宾催化剂载体及非均相催化剂

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2763938B1 (fr) *	1997-05-27	1999-10-22	Inst Francais Du Petrole	Procede pour l'hydroformylation d'olefines
US6403802B1 (en) *	1998-09-10	2002-06-11	University Of New Orleans Research & Technology Foundation	Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions
US6316380B1 (en) *	1998-09-10	2001-11-13	University Of New Orleans Research & Technology Foundation	Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene
US6362357B1 (en) *	1999-02-22	2002-03-26	University Of New Orleans Research & Technology Foundation	Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions
US6369265B1 (en) *	1999-09-16	2002-04-09	University Of New Orleans Research & Technology Foundation	Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions
WO2001036003A2 (en) *	1999-11-15	2001-05-25	Drug Innovation & Design, Inc.	Selective cellular targeting: multifunctional delivery vehicles
US6586599B1 (en) *	2000-04-20	2003-07-01	University Of New Orleans Research And Technology Foundation	Catalyzed coupling reactions of aryl halides with silanes
DE10300125A1 (de) *	2003-01-07	2004-07-15	Bayer Ag	Verfahren zur Herstellung von Nitrodiphenylaminen

2003
- 2003-01-07 DE DE10300098A patent/DE10300098A1/de not_active Withdrawn
- 2003-12-30 ES ES03029974T patent/ES2268269T3/es not_active Expired - Lifetime
- 2003-12-30 AT AT03029974T patent/ATE331721T1/de not_active IP Right Cessation
- 2003-12-30 EP EP03029974A patent/EP1437355B1/de not_active Expired - Lifetime
- 2003-12-30 DE DE50304043T patent/DE50304043D1/de not_active Expired - Fee Related
2004
- 2004-01-06 US US10/752,353 patent/US20040192664A1/en not_active Abandoned
- 2004-01-07 CN CNA2004100025166A patent/CN1517351A/zh active Pending

Also Published As

Publication number	Publication date
EP1437355A1 (de)	2004-07-14
US20040192664A1 (en)	2004-09-30
DE50304043D1 (de)	2006-08-10
ATE331721T1 (de)	2006-07-15
CN1517351A (zh)	2004-08-04
DE10300098A1 (de)	2004-07-15
EP1437355B1 (de)	2006-06-28

Publication	Publication Date	Title
ES2268269T3 (es)	2007-03-16	Complejos cobre-carbeno y su uso.
Bruno et al.	2013	Design and preparation of new palladium precatalysts for C–C and C–N cross-coupling reactions
Pratihar et al.	2019	Tetradentate amido azo Schiff base Cu (II), Ni (II) and Pd (II) complexes: Synthesis, characterization, spectral properties, and applications to catalysis in C–C coupling and oxidation reaction
ES2259128T3 (es)	2006-09-16	Complejos de cobre y su uso.
US5831128A (en)	1998-11-03	Synthesis of aromatic amines from chloroamatics
Pratihar et al.	2017	Azo-amide palladium (II) complexes: synthesis, characterization and application in C–C cross-coupling reactions
AU2018260728B2 (en)	2022-07-21	Process for the preparation of deuterated ethanol from D2
Hiwatari et al.	2004	Selective oxidative carbonylation of amines to oxamides and ureas catalyzed by palladium complexes
Pattanayak et al.	2014	Synthesis, characterization, structure and properties of copper and palladium complexes incorporating azo-amide ligands
ES2261575T3 (es)	2006-11-16	Complejos de carbenos n-heterociclicos y su uso.
CN103044491A (zh)	2013-04-17	甲醇与二氧化碳合成碳酸二甲酯的方法
CN109503604A (zh)	2019-03-22	苯并咪唑并咪唑衍生物及其合成方法
Yilmaz et al.	2003	Synthesis, Spectral and Thermal Studies of BIS-2, 6-Dimethanolpyridine Complexes of Co (II), Ni (II), Cu (II) and Zn (II) Saccharinates: Crystal Structures of [Ni (dmpy) 2](sac) 2· 2H2O and [Zn (dmpy) 2](sac) 2· 2H2O
EP3066064B1 (de)	2018-07-18	Cyclopropanierung
RU2420515C2 (ru)	2011-06-10	Способ получения 3,4,5-трифторанилина
US20040142820A1 (en)	2004-07-22	Pyrazolylarylalkines
US7276630B2 (en)	2007-10-02	Process for coupling benzylamines with haloaromatics
CN106977435A (zh)	2017-07-25	一种医药中间体羰基取代芳基硫醚化合物的合成方法
KR101582955B1 (ko)	2016-01-07	아닐린 유도체의 제조방법
CN102040563B (zh)	2014-04-16	一种3-芳基苯并[d]异噻唑的制备方法
Chu et al.	1999	Synthesis, crystal structure and characterization of ternary complexes of lanthanide (III) 3, 5-di-tert-butyl-γ-resorcylate with substituted pyridine-N-oxide
CN106883165A (zh)	2017-06-23	一种模板剂中间体的制备方法
CN106045916A (zh)	2016-10-26	一种咪唑酮类化合物的合成方法
Islam et al.	2010	A recyclable heterogeneous copper (II) Schiff base catalyst for the O-arylation reaction of phenols with aryl halides
KR101669646B1 (ko)	2016-11-09	4-니트로소아닐린의 제조방법